“Looking back at the early days of your company, what was the biggest risk you took when launching your business, and how did it shape your direction today?”
Here is what 4 thought leaders had to say.
Enter in Complex Industry
The biggest risk I took when launching Insuranks was challenging an industry built on complexity, opacity, and mistrust. Insurance isn’t exactly known for transparency, and creating a platform that empowers users to compare, review, and understand policies in plain language meant disrupting deeply entrenched systems.
I knew that insurers might be hesitant to embrace such openness and that trust from users wouldn’t come overnight. But I believed that if we put the power back in consumers’ hands, we could change how people interact with insurance for good.
The impact? Today, Insuranks reaches thousands of users monthly, helping them confidently make smarter coverage decisions. That initial risk of standing up for transparency in a guarded industry ultimately became our strongest differentiator.
Ofir Sahar, Founder, Insuranks
Company’s Excellence Standards
Early on, the biggest risk I took launching Merehead was doubling down on blockchain and fintech at a time when both were misunderstood by most business leaders. We had zero outside funding, so we used every saved penny to build a small, nimble team of developers and business analysts to tackle this murky space. That meant going after clients who needed serious technical leadership in areas like crypto exchanges, smart contracts, and decentralized finance—even though few knew what those terms meant.
One early example: we committed to building a token-based lending platform for a small European bank. Regulators, security doubts, nascent tooling—everything was up in the air. It was uncharted territory. We ended up building multiple prototypes, facing legal delays, and rewriting core modules half a dozen times. It took six months longer and cost far more than anyone expected.
But here’s why it mattered: that pressure forced us to build impeccable documentation, audit-ready code, and compliance-first processes—before it was ‘cool’ to care about those things. It shaped our direction into what we are today: a company known for pragmatic innovation, deeply trusting client partnerships, and zero tolerance for sloppy execution. That early grind—and that leap into the unknown—is still our north star when deciding which projects to take on.
Eugene Musienko, CEO, Merehead LLC
Leap Without Safety Net Creates Focused Solution
The biggest risk I took was quitting my steady job to work on something that didn’t yet exist. There was no guarantee it would work—just a rough idea that creating presentations could be easier, smarter, and a lot less painful.
I didn’t come from a big tech background or have a runway of investors cheering me on. It was just me, a savings account, and this nagging feeling that I had to try. That kind of leap is terrifying. There’s no backup plan, no safety net—just long days of building, testing, doubting, and doing it all over again.
But that risk forced me to focus. It made me build something real and useful, not just something that looked good on a pitch deck. I think that early pressure shaped the way I work today—listening more, overthinking less, and staying close to the actual problems people are trying to solve.
Diana Babaeva, Founder & CEO, AI presentation maker
Toolbox and Trust Build Pool Service Success
Looking back at the early days of 3G Pool Services, the biggest risk I took was leaving a steady job to launch a company with nothing but a toolbox, a pickup truck, and a promise to deliver reliable, high-quality pool care. There was no safety net—just grit, late nights, and a belief that consistency and integrity would set us apart.
That leap shaped everything about our direction today. It taught me that building trust with customers isn’t just part of the business—it’s the business. Every pool we service now reflects that same commitment I made on day one: to treat every backyard like it’s our own and to never cut corners, no matter how tempting the shortcut.
Ross Wilbur, BUSINESS OWNER,